110271-41-5Relevant academic research and scientific papers
Synthesis of two naphthoquinone antibiotics pentalongin and psychorubrin
Kesteleyn, Bart,De Kimpe, Norbert,Van Puyvelde, Luc
, p. 1881 - 1883 (1999)
The synthesis of two naturally occurring pyranonaphthoquinone antibiotics, pentalongin (1) and psychombrin (2), is reported.
Simple synthesis of two naphthoquinone antibiotics psychorubrin and pentalongin
Bulbule, Vivek J.,Koranne, Priti S.,Munot, Yogesh S.,Borate, Hanumant B.,Deshpande, Vishnu H.
, p. 587 - 594 (2003)
1H-Naphtho[2,3-c]pyran-5,10-dione derivatives were synthesized using chloromethylation of substituted-2-naphthylacetic acid as the key step. The utility of this method was demonstrated in the synthesis of two-pyranonaphthoquinone antibiotics psychorubrin (1) and pentalongin (2).
Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether
Nguyen Van, Tuyen,De Kimpe, Norbert
, p. 3443 - 3446 (2004)
The synthesis of two antibiotic pyranonaphthoquinones was performed by a straightforward synthetic route utilizing ring closing metathesis. Vinylation of 3-(1-propenyl)-2-hydroxymethyl-1,4-dimethoxynaphthalene under iridium catalysis and subsequent ring closing metathesis of 3-(1-propenyl)-2-vinyloxymethyl-1,4- dimethoxynaphthalene with Grubbs' catalyst paved the way to the natural antibiotics pentalongin and psychorubrin.
Total synthesis of two naphthoquinone antibiotics, psychorubrin and pentalongin, and their C(1)-substituted alkyl and aryl derivatives
Kesteleyn,De Kimpe,Van Puyvelde
, p. 1173 - 1179 (1999)
The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10- diones, bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux- Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10- dimethoxy-1H-naphtho[2,3-c]pyran-3-oles to the corresponding 3,4-dihydro-3- hydroxy- 1H-naphtho[2,3-c]pyran-5,10-diones gave, after acid-catalyzed dehydration, the desired 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid- catalyzed condensation of (3-hydroxymethyl-1,4-naphthoquinone-2- yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.
